Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Cyclopropylboronic acid | HCID 2760897 | — |
| Reactant | 6-Chloro-2-methoxypyridine-3-carbaldehyde | HCID 10855945 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 83816695 | HCID 83816695 | 58.6% |
Reaction Steps
6-Chloro-2-methoxynicotinaldehyde (200 mg, 1.17 mmol), cyclopropylboronic acid (200 mg, 2.33 mmol), sodium carbonate (371 mg, 3.50 mmol) and tetrakis(triphenylphosphine)palladium (0) (67.3 mg, 0.0583 mmol) were combined, diluted with toluene (2 mL) and water (200 μL). The reaction vial was purged with argon, heated to 90° C. and stirred for 12 hours. The reaction was cooled, loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 6-cyclopropyl-2-methoxynicotinaldehyde (121 mg, 0.683 mmol, 58.6% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08785445B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-1f48e00462e0466192a67ab55b345afe |
|---|
| Source note | uspto-grants-2014_07 |
|---|
